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United States Patent |
5,102,443
|
Kehne
,   et al.
|
April 7, 1992
|
Heterocyclically substituted phenoxysulfonylureas, and the use thereof
as herbicides or plant growth regulators
Abstract
Heterocyclically substituted phenoxysulfonylureas, processes for the
preparation thereof, and the use thereof as herbicides or plant growth
regulators. Compounds of the formula I or the salts thereof
##STR1##
where R.sup.1 is (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl or
(C.sub.2 -C.sub.8)alkynyl, these radicals being substituted by halogen,
saturated or unsaturated (C.sub.1 -C.sub.6)alkoxy, (C.sub.1
-C.sub.6)alkylthio, -sulfinyl or -sulfonyl, (C.sub.1
-C.sub.6)alkoxycarbonyl, NO.sub.2, CN or phenyl; furthermore is (C.sub.2
-C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl or (C.sub.3
-C.sub.8)cycloalkyl, which can be substituted by halogen or by alkoxy or
alkylthio; (C.sub.5 -C.sub.8)cycloalkenyl, cyclopropylmethyl, epoxypropyl;
furfuryl, tetrahydrofurfuryl or phenoxy (C.sub.1 -C.sub.4)alkyl, it being
possible for the last three substituents mentioned to be substituted by
halogen, alkyl or alkoxy; or phenyl which can be substituted by halogen,
alkyl, alkoxy, NO.sub.2, CF.sub.3, CN or OCHF.sub.2 ; or, in the event
that R.sup.2 is alkenyl, alkynyl, phenyl or phenoxy, each of which can be
substituted as indicated below, alkylsulfonyl or alkylsulfinyl and
n.noteq., R.sup.1 is also (C.sub.1 -C.sub.8)alkyl,
R.sup.2 radicals independently of one another are (C.sub.1 -C.sub.8)-alkyl,
(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, phenyl, phenoxy,
(C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1
-C.sub.4)-alkoxycarbonyl, (C.sub.2 -C.sub.4)alkenyloxycarbonyl, (C.sub.2 -
C.sub.4)alkynyloxycarbonyl, it being possible for all the abovementioned
radicals to be substituted by halogen, (C.sub.1 -C.sub.4)alkoxy or
(C.sub.1 -C.sub.4)alkylthio; furthermore halogen, NO.sub.2, (C.sub.1
-C.sub.4)alkylsulfonyl or (C.sub.1 -C.sub.4)alkylsulfinyl;
n is 0, 1, 2 or 3; y is O or S;
R.sup.3 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl,
(C.sub.3 -C.sub.8)-alkynyl or (C.sub.1 -C.sub.4)alkoxy;
R.sup.4 is a heterocyclic radical of the formulae
##STR2##
E is CH or N, G is O or CH.sub.2,
R.sup.5 and R.sup.6 are hydrogen, halogen, alkyl, alkoxy or alkylthio, it
being possible for the abovementioned alkyl-containing radicals to be
substituted by halogen, alkoxy or alkylthio, furthermore a radical of the
formula --NR.sup.12 R.sup.13, --OCHR.sup.7 --CO.sub.2 R.sup.12,
cycloalkyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy,
R.sup.7 is hydrogen or alkyl; R.sup.8 is alkyl, --CHF.sub.2 or --CH.sub.2
CF;
R.sup.9 and R.sup.10 are hydrogen, alkyl, alkoxy or halogen, R.sup.11 is
hydrogen, alkyl, --CHF.sub.2 or CH.sub.2 CF.sub.3, and R.sup.12 and
R.sup.13 are hydrogen, alkyl, alkenyl or alkynyl, have outstanding
herbicidal and plant growth-regulating properties.
Inventors:
|
Kehne; Heinz (Hofheim am Taunus, DE);
Willms; Lothar (Hillscheid, DE);
Bauer; Klaus (Hanauein/Taunus, DE);
Bieringer; Hermann (Eppstein/Taunus, DE);
Burstell; Helmut (Frankfurt am Main, DE)
|
Assignee:
|
Hoechst Aktiengesellschaft (Frankfurt, DE)
|
Appl. No.:
|
351958 |
Filed:
|
May 15, 1989 |
Foreign Application Priority Data
Current U.S. Class: |
504/214; 504/178; 504/211; 504/212; 504/213; 504/215; 544/321; 544/323; 544/324; 544/327; 544/331; 544/332; 544/333; 544/334; 544/335 |
Intern'l Class: |
A01N 043/54; C07D 239/42; C07D 239/26; C07D 239/69 |
Field of Search: |
71/92
544/321,324,323,327,331,332,333,334,335
|
References Cited
U.S. Patent Documents
4394153 | Jul., 1983 | Reap | 71/92.
|
4581059 | Apr., 1986 | Adams et al. | 71/92.
|
4678500 | Jul., 1987 | Hay et al. | 71/92.
|
Foreign Patent Documents |
62-277306 | Feb., 1987 | JP.
| |
62-155202 | Oct., 1987 | JP.
| |
Other References
Kato et al., Chemical Abstracts 108:200229s (1988).
Kato et al., Chemical Abstracts 108:33622f (1988).
|
Primary Examiner: Ford; John M.
Attorney, Agent or Firm: Curtis, Morris & Safford, P.C.
Claims
We claim:
1. A compound of formula I or a salt thereof
##STR21##
where R.sup.1 is (C.sub.2 -C.sub.8)alkenyl;
(C.sub.2 -C.sub.8)alkynyl;
(C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl or (C.sub.2
-C.sub.8)alkynyl, each of which is monosubstituted or polysubstituted by
chloro or monosubstituted or disubstituted by (C.sub.1 -C.sub.6)alkoxy,
(C.sub.2 -C.sub.6)alkenyloxy, (C.sub.2 -C.sub.6)alkynyloxy, (C.sub.1
-C.sub.6)alkylthio, (C.sub.1 -C.sub.6)alkylsulfinyl, (C.sub.1
-C.sub.6)alkysulfonyl, (C.sub.1 -C.sub.6)alkoxycarbonyl, NO.sub.2, CN or
by phenyl;
(C.sub.3 -C.sub.8)cycloalkyl which can be monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.4)alkoxy or
(C.sub.1 -C.sub.4)alkylthio;
(C.sub.5 -C.sub.8)cycloalkenyl, cyclopropylmethyl or epoxypropyl;
furfuryl, tetrahydrofurfuryl or phenoxy-(C.sub.1 -C.sub.4)alkyl, each of
which can be substituted by halogen, (C.sub.1 -C.sub.4)alkyl or (C.sub.1
-C.sub.4)alkoxy; or
phenyl which can be monosubstituted or polysubstituted by halogen, (C.sub.1
-C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, NO.sub.2, CF.sub.3, CN or
OCHF.sub.2 ;
or in the event that R.sup.2 is (C.sub.2 -C.sub.8)alkenyl, (C.sub.2
-C.sub.8)alkynyl, phenyl or phenoxy, each of which can be substituted as
indicated below, or R.sup.2 is (C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1
-C.sub.4)alkylsulfinyl, and further n.noteq.0, then R.sup.1 can also be
(C.sub.1 -C.sub.8)alkyl;
R.sup.2 is, each independently of any other R.sub.2 when n>1, (C.sub.1
-C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl,
phenyl, phenoxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio,
(C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.2 -C.sub.4)alkenyloxycarbonyl or
(C.sub.2 -C.sub.4)alkynyloxycarbonyl, each of which can be monosubstituted
or polysubstituted by halogen or monosubstituted or disubstituted by
(C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio; or
is halogen, NO.sub.2, (C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1
-C.sub.4)alkylsulfinyl;
n is 0, 1, 2 or 3;
Y is O or S;
R.sup.3 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl,
(C.sub.3 -C.sub.8)-alkynyl or (C.sub.1 -C.sub.4)alkoxy;
R.sup.4 is a heterocyclic radical of formula
##STR22##
R.sup.5 and R.sup.6, independently of one another, are hydrogen or
halogen;
(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy or (C.sub.1
-C.sub.6)alkylthio, each of which can be monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.4)alkoxy or
(C.sub.1 -C.sub.4)alkylthio;
or are a radical of the formula --NR.sup.12 R.sup.13, --OCHR.sup.7
--CO.sub.2 R.sup.12, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.3
-C.sub.5)alkenyl, (C.sub.2 -C.sub.5)alkynyl, (C.sub.3 -C.sub.5)alkenyloxy
or (C.sub.3 -C.sub.5)alkynyloxy;
R.sup.7 is hydrogen or (C.sub.1 -C.sub.4)alkyl; and
R.sup.12 and R.sup.13, independently of one another, are hydrogen, (C.sub.1
-C.sub.4)alkyl, (C.sub.2 -C.sub.4)alkenyl or (C.sub.3 -C.sub.4)alkynyl.
2. A compound of formula I or a salt thereof
##STR23##
where R.sup.1 is (C.sub.2 -C.sub.8)alkenyl;
(C.sub.2 -C.sub.8)alkynyl;
(C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl or (C.sub.2
-C.sub.8)alkynyl, each of which is monosubstituted or disubstituted by
(C.sub.1 -C.sub.6)alkoxy, (C.sub.2 -C.sub.6)alkenyloxy, (C.sub.2
-C.sub.6)alkynyloxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1
-C.sub.6)alkylsulfinyl, (C.sub.1 -C.sub.6)alkylsulfonyl, (C.sub.1
-C.sub.6)alkoxycarbonyl, NO.sub.2, CN or by phenyl;
(C.sub.3 -C.sub.8)cycloalkyl which can be monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.4)alkoxy or
(C.sub.1 -C.sub.4)alkylthio;
(C.sub.5 -C.sub.8)cycloalkenyl, cyclopropylmethyl or epoxypropyl;
furfuryl, tetrahydrofurfuryl or phenoxy-(C.sub.1 -C.sub.4)alkyl, each of
which can be substituted by halogen, (C.sub.1 -C.sub.4)alkyl or (C.sub.1
-C.sub.4)alkoxy; or phenyl which can be monosubstituted or polysubstituted
by halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, NO.sub.2,
CF.sub.3, CN or OCHF.sub.2 ;
or in the event that R.sup.2 is (C.sub.2 -C.sub.8)alkenyl, (C.sub.2
-C.sub.8)alkynyl, phenyl or phenoxy, each of which can be substituted as
indicated below, or R.sup.2 is (C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1
-C.sub.4)alkylsulfinyl, and further n.noteq.0, then R.sup.1 can also be
(C.sub.1 -C.sub.8)alkyl;
R.sup.2 is, each independently of any other R.sub.2 when n>1, (C.sub.1
-C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl,
phenyl, phenoxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio,
(C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.2 -C.sub.4)alkenyloxycarbonyl or
(C.sub.2 -C.sub.4)alkynyloxycarbonyl, each of which can be monosubstituted
or polysubstituted by halogen or monosubstituted or disubstituted by
(C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio; or is halogen,
NO.sub.2, (C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1
-C.sub.4)alkylsulfinyl;
n is 0, 1, 2 or 3;
Y is O or S;
R.sup.3 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl,
(C.sub.3 -C.sub.8)-alkynyl or (C.sub.1 -C.sub.4)alkoxy;
R.sup.4 is a heterocyclic radical of formula
##STR24##
R.sup.5 and R.sup.6, independently of one another, are hydrogen or
halogen;
(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy or (C.sub.1
-C.sub.6)alkylthio, each of which can be monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio;
or are a radical of the formula --NR.sup.12 R.sup.13, --OCHR.sup.7
--CO.sub.2 R.sup.12, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.3
-C.sub.5)alkenyl, (C.sub.2 -C.sub.4)alkynyl, (C.sub.3 -C.sub.5)alkenyloxy
or (C.sub.3 -C.sub.5)alkynyloxy;
R.sup.7 is hydrogen or (C.sub.1 -C.sub.4)alkyl; and
R.sup.12 and R.sup.13, independently of one another, are hydrogen, (C.sub.1
-C.sub.4)alkyl, (C.sub.2 -C.sub.4)alkenyl or (C.sub.3 -C.sub.4)alkynyl.
3. A compound of formula I or a salt thereof
##STR25##
where R.sup.1 is (C.sub.2 -C.sub.8)alkenyl;
(C.sub.2 -C.sub.8)alkynyl;
(C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl or (C.sub.2
-C.sub.8)alkynyl, each of which is monosubstituted or polysubstituted by
chloro or bromo or monosubstituted or disubstituted by (C.sub.1
-C.sub.6)alkoxy, (C.sub.2 -C.sub.6)alkenyloxy, (C.sub.2
-C.sub.6)-alkynyloxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1
-C.sub.6)alkylsulfinyl, (C.sub.1 -C.sub.6)alkylsulfonyl, (C.sub.1
-C.sub.6)alkoxycarbonyl, NO.sub.2, CN or by phenyl;
(C.sub.3 -C.sub.8)cycloalkyl which can be monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio;
(C.sub.5 -C.sub.8)cycloalkenyl, cyclopropylmethyl or epoxypropyl;
furfuryl, tetrahydrofurfuryl or phenoxy-(C.sub.1 -C.sub.4)alkyl, each of
which can be substituted by halogen, (C.sub.1 -C.sub.4)alkyl or (C.sub.1
-C.sub.4)alkoxy; or
phenyl which can be monosubstituted or polysubstituted by halogen, (C.sub.1
-C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, NO.sub.2, CF.sub.3, CN or
OCHF.sub.2 ;
or in the event that R.sup.2 is (C.sub.2 -C.sub.8)alkenyl, (C.sub.2
-C.sub.8)-alkynyl, phenyl or phenoxy, each of which can be substituted as
indicated below, or R.sup.2 is (C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1
-C.sub.4)alkylsulfinyl, and further n.noteq.0, then R.sup.1 can also be
(C.sub.1 -C.sub.8)alkyl;
R.sup.2 is, each independently of any other R.sub.2 when n>1, (C.sub.1
-C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl,
phenyl, phenoxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio,
(C.sub.1 -C.sub.4)-alkoxycarbonyl, (C.sub.2 -C.sub.4)alkenyloxycarbonyl or
(C.sub.2 -C.sub.4)-alkynyloxycarbonyl, each of which can be
monosubstituted or polysubstituted by halogen or monosubstituted or
disubstituted by (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio;
or
is halogen, NO.sub.2, (C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1
-C.sub.4)alkylsulfinyl;
n is 0, 1, 2 or 3;
Y is O or S;
R.sup.3 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl,
(C.sub.3 -C.sub.8)-alkynyl or (C.sub.1 -C.sub.4)alkoxy;
R.sup.4 is a heterocyclic radical of formula
##STR26##
R.sup.5 and R.sup.6, independently of one another, are hydrogen or
halogen;
(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy or (C.sub.1
-C.sub.6)alkylthio, each of which can be monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio; or are a radical of the
formula --NR.sup.12 R.sup.13, --OCHR.sup.7 --CO.sub.2 R.sup.12, (C.sub.3
-C.sub.6)cycloalkyl, (C.sub.3 -C.sub.5)alkenyl, (C.sub.2 -C.sub.4)alkynyl,
(C.sub.3 -C.sub.5)alkenyloxy or (C.sub.3 -C.sub.5)alkynyloxy;
R.sup.7 is hydrogen or (C.sub.1 -C.sub.4)alkyl; and
R.sup.12 and R.sup.13, independently of one another, are hydrogen, (C.sub.1
-C.sub.4)alkyl, (C.sub.2 -C.sub.4)alkenyl or (C.sub.3 -C.sub.4)alkynyl.
4. A compound of the formula I of claim 3 or a salt thereof, where R.sup.1
is
(C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.5)alkenyl or (C.sub.2
-C.sub.4)alkynyl, each of which is monosubstituted or polysubstituted by
chloro or bromo or monosubstituted or disubstituted by (C.sub.1
-C.sub.6)alkoxy, (C.sub.2 -C.sub.6)alkenyloxy, (C.sub.2
-C.sub.6)-alkynyloxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1
-C.sub.6)alkylsulfinyl, (C.sub.1 -C.sub.6)alkylsulfonyl, (C.sub.1
-C.sub.6)alkoxycarbonyl, NO.sub.2, CN or by phenyl, or
(C.sub.2 -C.sub.5)alkenyl or (C.sub.2 -C.sub.4)alkynyl or, in the event
that n=1 and R.sup.2 is (C.sub.2 -C.sub.8)alkenyl or (C.sub.2
-C.sub.8)alkynyl, then R.sup.1 can also be (C.sub.1 -C.sub.4)alkyl;
R.sup.2 is (C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.5)alkenyl, (C.sub.2
-C.sub.4)alkynyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, phenyl, phenoxy,
(C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio, each of which can
be monosubstituted or polysubstitued by halogen or monosubstituted or
disubstituted by (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkythio,
or
is halogen;
n is 0, 1 or 2;
Y is O;
R.sup.3 is hydrogen, (C.sub.1 -C.sub.4)alkyl or (C.sub.3 -C.sub.4)alkenyl;
R.sup.4 is a heterocyclic radical of the formula
##STR27##
R.sup.5 and R.sup.6 independently of one another are halogen, or (C.sub.1
-C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio,
each of which can be monosubstituted or poly substituted by halogen or
monosubstituted or disubstituted by (C.sub.1 -C.sub.4)alkoxy or (C.sub.1
-C.sub.4)alkylthio.
5. A compound of the formula I of claim 3 or a salt thereof, where R.sup.1
is (C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.5)alkenyl, or (C.sub.2
-C.sub.4)alkynyl, each of which is monosubstituted or polysubstituted by
chloro or bromo or monosubstituted or disubstituted by (C.sub.1
-C.sub.6)alkoxy, (C.sub.2 -C.sub.6)alkenyloxy, (C.sub.2
-C.sub.6)-alkynyloxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1
-C.sub.6)alkylsulfinyl, (C.sub.1 -C.sub.6)alkylsulfonyl, (C.sub.1
-C.sub.6)alkoxycarbonyl, NO.sub.2, CN or by phenyl, or
(C.sub.2 -C.sub.5)alkenyl or (C.sub.2 -C.sub.4)alkynyl;
R.sup.2 is (C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.5)alkenyl, (C.sub.1
-C.sub.4)alkoxycarbonyl, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1
-C.sub.4)alkylthio, each of which can be monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkythio), or
is fluorine or chlorine,
n=0 or 1,
R.sup.3 is hydrogen or methyl,
R.sup.4 is a heterocyclic radical of the formula
##STR28##
and R.sup.5 and R.sup.6 independently of one another are chlorine,
bromine, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, OCHF.sub.2,
OCH.sub.2 CF.sub.3 or CF.sub.3.
6. A herbicidal composition containing an effective herbicidal amount of
one or more compounds of the formula I or salts thereof as claimed in
claim 3 and inert auxilaries.
7. A plant growth-regulating composition containing an effective
plant-growth regulating amount of one or more compounds of the formula I
or salts thereof as claimed in claim 3 and inert auxiliaries.
8. A method of controlling weed plants, which comprises applying an
effective amount of one or more compounds of the formula I or salts
thereof, as claimed in claim 3, to these weed plants or the soil used for
agriculture or industry.
9. A method of regulating the growth of crop plants which comprises
applying an effective amount of one or more compounds of the formula I or
salts thereof, as claimed in claim 3, to these crop plants or the cropped
area.
10. 1-
[2-(2-chloroethoxy)phenoxysulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea.
11. 3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-propargyloxyphenoxysulfonyl)urea.
12. 3-(4,6-dimethoxypyrimidin-2-yl)-1-[2-(2-methoxyethoxy)-phenoxysulfonyl]
urea.
13. A compound of formula I, as claimed in claim 3, wherein R.sup.1 is
CH.sub.2 CH.sub.2 OCH.sub.3, R.sup.3 is H, R.sup.4 is
##STR29##
R.sup.5 is CH.sub.3, R.sup.6 is CH.sub.3, n is 0 and Y is O.
14. A compound of formula I, as claimed in claim 3, wherein
R.sup.1 is CH.sub.2 CH.dbd.CH.sub.2, R.sup.3 is H, R.sup.4 is
##STR30##
R.sup.5 is CH.sub.3, R.sup.6 is CH.sub.3, n is 0 and Y is O.
15. A compound of formula I, as claimed in claim 3, wherein R.sup.1 is
CH.sub.2 CH.dbd.CH.sub.2, R.sup.3 is H, R.sup.4 is
##STR31##
R.sup.5 is OCH.sub.3, R.sup.6 is CH.sub.3, n is 0 and Y is O.
16. A compound of formula I, as claimed in claim 3, wherein R.sup.1 is
CH.sub.2 CH.dbd.CH.sub.2, R.sup.3 is H, R.sup.4 is
##STR32##
R.sup.5 is OCH.sub.3, R.sup.6 is OCH.sub.3, n is 0 and Y is O.
Description
It is known that heterocyclically substituted phenoxysulfonylureas possess
herbicidal and plant-growth regulating properties (EP-A 4,163, EP-A
113,956, DE-A 3,151-450).
It has now been found that heterocyclically substituted sulfamic acid
phenyl esters, the phenyl ester moiety of which is formed by specific
pyrocatechol monoethers, are particularly suitable as herbicides and plant
growth regulators.
The present invention therefore relates to compounds of the formula (I) or
salts thereof
##STR3##
where R.sup.1 is (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl,
(C.sub.2 -C.sub.8)alkynyl, each of these radicals being monosubstituted or
polysubstituted by halogen or monosubstituted or disubstituted by (C.sub.1
-C.sub.6)alkoxy, (C.sub.2 -C.sub.6)alkenyloxy, (C.sub.2
-C.sub.6)-alkynyloxy, (C.sub.1 -C.sub.6)alkylthio, (C.sub.1
-C.sub.6)alkylsulfinyl, (C.sub.1 -C.sub.6)alkylsulfonyl, (C.sub.1
-C.sub.6)alkoxycarbonyl, NO.sub.2, CN or by phenyl; furthermore (C.sub.2
-C.sub.8)alkenyl, (C.sub.2 -C.sub.8)-alkynyl, (C.sub.3
-C.sub.8)cycloalkyl, which can be monosubstituted or polysubstituted by
halogen or monosubstituted or disubstituted by (C.sub.1 -C.sub.4)alkoxy or
(C.sub.1 -C.sub.4)alkylthio; (C.sub.5 -C.sub.8)cycloalkenyl,
cyclopropylmethyl, epoxypropyl; furfuryl, tetrahydrofurfuryl, phenoxy
(C.sub.1 -C.sub.4)alkyl, it being possible for the last three substituents
mentioned to be substituted by halogen, (C.sub.1 -C.sub.4)alkyl or
(C.sub.1 -C.sub.4)alkoxy; or phenyl which can be monosubstituted or
polysubstituted by halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1
-C.sub.4)alkoxy, NO.sub.2, CF.sub.3, CN or OCHF.sub.2 ; or in the event
that R.sup.2 is (C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)-alkynyl,
phenyl, phenoxy, each of which can be substituted as indicated below,
(C.sub.1 -C.sub.4)alkylsulfonyl or (C.sub.1 -C.sub.4)alkylsulfinyl and
n.noteq.0, R.sup.1 is also (C.sub.1 -C.sub.8)alkyl,
R.sup.2 radicals independently of one another are (C.sub.1 -C.sub.8)-alkyl,
(C.sub.2 -C.sub.8)alkenyl, (C.sub.2 -C.sub.8)alkynyl, phenyl, phenoxy,
(C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1
-C.sub.4)alkoxycarbonyl, (C.sub.2 -C.sub.4)alkenyloxycarbonyl or (C.sub.2
-C.sub.4)alkynyloxycarbonyl, it being possible for all of the
abovementioned radicals to be monosubstituted or polysubstituted by
halogen or monosubstituted to disubstituted by (C.sub.1 -C.sub.4)alkoxy or
(C.sub.1 -C.sub.4)alkylthio; furthermore are halogen, NO.sub.2, (C.sub.1
-C.sub.4)alkylsulfonyl or (C.sub.1 -C.sub.4)alkylsulfinyl;
n is 0, 1, 2 or 3;
Y is O or S;
R.sup.3 is hydrogen, (C.sub.1 -C.sub.8)alkyl, (C.sub.2 -C.sub.8)alkenyl,
(C.sub.3 -C.sub.8)-alkynyl or (C.sub.1 -C.sub.4)alkoxy;
R.sup.4 is a heterocyclic radical of the formulae
##STR4##
E is CH or N, G is O or CH.sub.2,
R.sup.5 and R.sup.6 independently of one another are hydrogen, halogen,
(C.sub.1 -C.sub.6) alkyl, (C.sub.1 -C.sub.6) alkoxy or (C.sub.1 -C.sub.6)
alkylthio, it being possible for the abovementioned alkyl-containing
radicals to be monosubstituted or polysubstituted by halogen or
monosubstituted or disubstituted by (C.sub.1 -C.sub.4) alkoxy or (C.sub.1
-C.sub.4)alkylthio, furthermore are a radical of the formula --NR.sup.12
R.sup.13, --OCHR.sup.7 --CO.sub.2 R.sup.12, (C.sub.3 -C.sub.6)cycloalkyl,
(C.sub.3 -C.sub.5)alkenyl, (C.sub.2 -C.sub.4)alkynyl, (C.sub.3
-C.sub.5)alkenyloxy, or (C.sub.3 -C.sub.5)alkynyloxy,
R.sup.7 is hydrogen or (C.sub.1 -C.sub.4)alkyl,
R.sup.8 is (C.sub.1 -C.sub.4)alkyl, --CHF.sub.2 or --CH.sub.2 CF.sub.3,
R.sup.9 and R.sup.10 independently of one another are hydrogen, (C.sub.1
-C.sub.4)alkyl, (C.sub.1 -C.sub.5)alkoxy or halogen,
R.sup.11 is hydrogen, (C.sub.1 -C.sub.4)alkyl, -CHF.sub.2 or CH.sub.2
CF.sub.3 and
R.sup.12 and R.sup.13 independently of one another are hydrogen, (C.sub.1
-C.sub.4)alkyl, (C.sub.2 -C.sub.4)alkenyl or (C.sub.3 -C.sub.4)alkynyl.
The compounds of the formula (I) can form salts in which the hydrogen of
the -SO.sub.2 -NH- group is replaced by a cation which is suitable for
agriculture. In general, these salts are metal salts, in particular alkali
metal salts, alkaline earth metal salts, optionally alkylated ammonium
salts or organic amine salts.
Preferred compounds of the formula (I) and salts thereof are those in which
R.sup.1 is (C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.5)alkenyl or (C.sub.2
-C.sub.4)alkynyl, these radicals being substituted as described above;
furthermore is (C.sub.2 -C.sub.5)alkenyl, (C.sub.2 -C.sub.4)alkynyl or, in
the event that n=1 and R.sup.2 is (C.sub.2 -C.sub.8)alkenyl or (C.sub.2
-C.sub.8)alkynyl, is (C.sub.1 -C.sub.4)alkyl; R.sup.2 is (C.sub.1
-C.sub.4)alkyl, (C.sub.2 -C.sub.5)alkenyl, (C.sub.2 -C.sub.4)alkynyl,
(C.sub.1 -C.sub.4)alkoxycarbonyl, phenyl, phenoxy, (C.sub.1
-C.sub.4)alkoxy or (C.sub.1 -C.sub.4)alkylthio, it being possible for
these radicals to be substituted as described above; or is halogen; n is
0, 1 or 2, Y is O, R.sup.3 is hydrogen, (C.sub.1 -C.sub.4)alkyl or
(C.sub.3 -C.sub.4)alkenyl, R.sup.4 is a heterocyclic radical of the
formula
##STR5##
E is CH or N, R.sup.5 and R.sup.6 independently of one another are
halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy or (C.sub.1
-C.sub.4)alkylthio, each of which can be substituted as described above.
Halogen is preferably fluorine, chlorine or bromine.
Particularly preferred compounds of the formula (I) and salts thereof are
those where R.sup.1 is (C.sub.1 -C.sub.4)alkyl, (C.sub.2 -C.sub.5)alkenyl
or (C.sub.2 -C.sub.4)alkynyl, these radicals being substituted as
described above, furthermore (C.sub.2 -C.sub.5)alkenyl or (C.sub.2
-C.sub.4)alkynyl; R.sup.2 is (C.sub.1 -C.sub.4)alkyl, (C.sub.2
-C.sub.5)alkenyl, (C.sub.1 -C.sub.4)alkoxycarbonyl, (C.sub.1
-C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio, each of which can be
substituted as described above; or is fluorine or chlorine, n=0 or 1,
R.sup.3 is hydrogen or methyl, R.sup.4 is a heterocyclic radical of the
formula
##STR6##
E is CH or N and R.sup.5 and R.sup.6 independently of one another are
chlorine, bromine, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy,
OCHF.sub.2, OCH.sub.2 CF.sub.3 or CF.sub.3.
The present invention also relates to processes for the preparation of
compounds of the general formula (I) or salts thereof, characterized in
that
(a) a compound of the formula (II)
##STR7##
is reacted with a compound of the formula (III)
##STR8##
or (b) a compound of the formula (IV)
##STR9##
is reacted with a chlorosulfonylurea of the formula (V)
##STR10##
or (c) a compound of the formula (VI)
##STR11##
is reacted with a carbamate of the formula (VII)
##STR12##
where Z is phenyl or (C.sub.1 -C.sub.6)alkyl, and, if desired, the
resulting compounds of the formula I are converted into their salts.
The compounds of the formulae (II) and (III) are preferably reacted in
inert aprotic solvents, such as, for example, acetonitrile,
dichloromethane, toluene, tetrahydrofuran or dioxane, at temperatures
between 0.degree. C. and the boiling point of the solvent.
The phenoxysulfonyl isocyanates of the formula (II) can be prepared in a
simple manner by processes which are known in principle from the
corresponding pyrocatechol monoethers of the formula (IV) and
chlorosulfonyl isocyanate (cf. G. Lohaus, Chem. Ber. 105, 2791 (1972)).
The starting substances of the formula (III) are known or can be prepared
by processes which are known in principle, for example by cyclizing
corresponding guanidine derivatives with appropriately substituted
1,3-diketones, cf., for example, "The Chemistry of Heterocyclic
Compounds", Vol. XVI (1962) and Supplement I (1970), or by derivatization
of cyanuric chloride, cf., for example, "The Chemistry of Heterocyclic
Compounds", L. Rapaport: "s-Triazines and Derivatives" (1959).
The reaction of the compounds (IV) with the chlorosulfonylureas (V) is
preferably carried out in inert solvents, such as, for example,
dichloromethane, at temperatures between -10.degree. C. and 80.degree. C.
in the presence of a base as the HCl-binding agent. Bases which can be
employed are alkali metal carbonates, alkali metal bicarbonates, alkaline
earth metal carbonates or alkaline earth metal bicarbonates, such as, for
example, K.sub.2 CO.sub.3, NaHCO.sub.3, Na.sub.2 CO.sub.3, or tertiary
amines, such as, for example, pyridine or triethylamine.
The pyrocatechol monothers (IV) are known from the literature or can be
prepared by processes which are known from the literature. The
chlorosulfonylureas (V) are accessible from the amines of the formula
(III) and chlorosulfonyl isocyanate (EP-A 141,199).
The reaction of the compounds (VI) with the heterocyclic carbamates of the
formula VII is preferably carried out in the presence of tertiary organic
bases, such as, for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), in
inert solvents, such as acetonitrile or dioxane, at temperatures between
20.degree. C. and the boiling point of the solvent (analogously to EP-A
44,807).
The carbamates (VII), which are required for this process, are known from
the literature or are prepared by known processes (EP-A 70,804). The
sulfamates (VI) are prepared from the pyrocatechol monoethers on which
they are based by known processes (cf., for example, Synthesis 1978, 357;
Z. Chem. 15, 270 (1975); Chem. Ber. 105, 2791 (1972)).
The salts of the compounds of the formula I are preferably prepared in
inert solvents, such as, for example, water, methanol or acetone, at
temperatures from 0.degree.-100.degree. C. Examples of bases which are
suitable for the preparation of the salts according to the invention are
alkali metal carbonates, such as potassium carbonate, alkali metal
hydroxides and alkaline earth metal hydroxides, ammonia or ethanolamine.
The compounds of the formula I according to the invention have an excellent
herbicidal activity against a broad range of economically important
monocotyledon and dicotyledon noxious plants. The active substances act
equally well on perennial weeds which produce shoots from rhizomes,
rootstocks or other perennial organs and which cannot be easily
controlled. In this context, it does not matter if the substances are
applied before sowing, as a pre-emergence treatment or post-emergence
treatment. Some representatives of the monocotyledon and dicotyledon weed
flora which can be controlled may be mentioned individually as examples,
but this is not to be taken to mean a restriction to certain species.
The monocotyledon weed species controlled include, for example, Avena,
Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria etc. and
Cyperus species from the annual group, and the perennial species include
Agropyron, Cynodon, Imperata and Sorghum etc., and also perennial Cyperus
species.
Of the dicotyledon weed species, the range of action covers species such
as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus,
Sinapis, Ipomoea, Matricaria, Abutilon, Sida etc. from the annual plants,
and Convolvulus, Cirsium, Rumex, Artemisia etc. from the perennials.
Excellent control of weeds occurring under the specific culture conditions
in rice, such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus,
Cyperus etc., by the active substances according to the invention is also
possible.
If the compounds according to the invention are applied to the soil surface
before germination, either emergence of the weed seedlings is prevented
completely, or the weeds grow until they have reached the cotyledon stage
but growth then comes to a standstill and, after a period of three to four
weeks, the plants eventually die completely. When, in the post-emergence
method, the active substances are applied to the green parts of the
plants, growth also stops dramatically very soon after the treatment, and
the weed plants remain in the growth stage of the time of application, or,
after a certain period of time, die more or less rapidly, so that
competition by the weeds, which is detrimental for the crop plants, can
thus be prevented at a very early stage and in a sustained manner by using
the novel agents according to the invention.
Even though the compounds according to the invention have an excellent
herbicidal activity against monocotyledon and dicotyledon weeds, crop
plants of economically important crops such as, for example, wheat,
barley, rye, rice, maize, sugar beet, cotton and soya beans, are damaged
only to a negligible extent, or not at all. Thus, the present compounds
are very suitable for selectively controlling undesired plant growth in
agricultural plantations of useful plants.
In addition, the compounds according to the invention have plant
growth-regulating properties in crop plants. They have a regulating effect
on the plant metabolism and can thus be employed for facilitating
harvesting, such as, for example, by provoking desiccation, abscission and
stunted growth. Furthermore, they are suitable for generally regulating
and inhibiting undesired vegetative growth, without simultaneously
destroying the plants. Inhibition of vegetative growth plays an important
role in many monocotyledon and dicotyledon crops because lodging can be
reduced hereby, or prevented completely.
The agents according to the invention can be employed in the conventional
preparations as wettable powders, emulsifiable concentrates, emulsions,
sprayable solutions, dusting agents, seed-dressing agents, dispersions,
granules or microgranules.
Wettable powders are preparations which are uniformly dispersible in water
and which, besides the active substance, also contain wetting agents, for
example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols,
alkylsulfonates or alkylphenylsulfonates, and dispersing agents, for
example, sodium ligninsulfonate, sodium
2,2'-dinaphthylmethane-6,6'-disulfonate, sodium
dibutylnaphthalenesulfonate and also sodium oleoylmethyltaurinate, as well
as, if appropriate, a diluent or inert substance. The formulations are
prepared in a customary manner, for example by grinding and mixing of the
components.
Emulsifiable concentrates can be prepared, for example, by dissolving the
active substances in an inert organic solvent, for example butanol,
cyclohexanone, dimethylformamide, xylene and also higher-boiling aromatics
or hydrocarbons, with the addition of one or more emulsifiers. In the case
of liquid active substances, all or part of the solvent component can be
omitted. Emulsifiers which can be used are, for example: calcium salts of
alkylarylsulfonic acid, such as Ca dodecylbenzenesulfonate, or nonionic
emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol
ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide
condensation products, fatty alcohol/propylene oxide/-ethylene oxide
condensation products, alkyl polyglycol ethers, sorbitan fatty acid
esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene
sorbitol esters.
Dusting agents are obtained by grinding the active substance with finely
divided solid substances, for example talc or natural clays, such as
kaolin, bentonite, pyrophillite, or diatomaceous earth.
Granules can be produced either by spraying the active substance onto
adsorptive, granulated inert material or by applying active substance
concentrates onto the surface of carriers such as sand, kaolinites or
granulated inert material, by means of binders, for example polyvinyl
alcohol, sodium polyacrylate or alternatively mineral oils. Suitable
active substances can also be granulated in the manner which is
conventional for the preparation of fertilizer granules, if desired in a
mixture with fertilizers.
The active substance concentration in wettable powders is, for example,
about 10 to 90% by weight; the remainder to 100% by weight comprises
conventional formulation components. In the case of emulsifiable
concentrates, the active substance concentration can be about 5 to 80% by
weight. Formulations in the form of dusts usually contain 5 to 20% by
weight, sprayable solutions about 2 to 20% by weight. In the case of
granules, the active substance content depends partly on whether the
active compound is liquid or solid and on which granulation auxiliaries,
fillers etc. are used.
In addition, the active substance formulations mentioned contain, if
appropriate, the adhesives, wetting agents, dispersing agents,
emulsifiers, penetrants, solvents, fillers or carriers which are
conventional in each case.
For use, the concentrates, present in commercially available form, are
diluted, if appropriate, in a conventional manner, for example using water
in the case of wettable powders, emulsifiable concentrates, dispersions
and, in some cases, also in the case of microgranules. Preparations in the
form of dusts and in the form of granules and also sprayable solutions are
usually not further diluted with other inert substances before use.
The application rate required varies with the external conditions, such as
temperature, humidity amongst others. It can vary within wide limits, for
example between 0.005 and 10.0 kg/ha or more of active substance,
preferably, however, it is between 0.01 and 5 kg/ha.
If appropriate, mixtures or mixed formulations with other active
substances, such as, for example, insecticides, acaricides, herbicides,
fertilizers, growth regulators or fungicides are also possible.
The following examples illustrate the invention in greater detail.
FORMULATION EXAMPLES
A. A dusting agent is obtained by mixing 10 parts by weight of active
substance and 90 parts by weight of talc or inert substance, and
comminuting the mixture in a hammer mill.
B. A wettable powder which is readily dispersible in water is obtained by
mixing 25 parts by weight of active substance, 64 parts by weight of
kaolin-containing quartz as inert substance, 10 parts by weight of
potassium ligninsulfonate and 1 part by weight of sodium
oleoylmethyltaurinate as wetting and dispersing agent, and grinding the
mixture in a pinned disk mill.
C. A dispersion concentrate which is readily dispersible in water is
obtained by mixing 20 parts by weight of active substance with 6 parts by
weight of alkylphenol polyglycol ether (.RTM.Triton X 207), 3 parts by
weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of
paraffinic mineral oil (boiling range, for example, about 255.degree. to
above 377.degree. C.), and grinding the mixture in a ball mill to a
fineness of below 5 microns.
D. An emulsifiable concentrate is obtained from 15 parts by weight of
active substance, 75 parts by weight of cyclohexanone as solvent and 10
parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.
CHEMICAL EXAMPLES
Example 1
2-(2-Chloroethoxy)phenoxysulfonyl isocyanate
3.4 g (0.024 mol) of chlorosulfonyl isocyanate are added dropwise at
25.degree. C. to a solution of 3.45 g (0.02 mol) of
2-(2-chloroethoxy)phenol in 20 ml of xylene. When the dropwise addition is
complete, the temperature is increased slowly to 140.degree. C., and the
mixture is refluxed for 2 hours. The mixture is cooled and the solvent as
well as excess chlorosulfonyl isocyanate are removed on a rotary
evaporator. The yellow oil which remains (5.6 g=100% of theory) is
employed without further purification.
Example 2
1-[2-(2-Chloroethoxy)phenoxysulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea
A solution of 5.6 g (0.02 mol) of the product of Example 1 in 20 ml of
dichloromethane is added dropwise at 0.degree. C. to 3.1 g (0.02 mol) of
2-amino-4,6-dimethoxypyrimidine in 30 ml of dichloromethane. The reaction
mixture is allowed to reach room temperature, and stirring is continued
for 24 hours. The reaction solution is diluted using 100 ml of
dichloromethane and washed with 50 ml of 1N hydrochloric acid and 50 ml of
water. The organic phase is dried using sodium sulfate, and the solvent is
removed on a rotary evaporator. The viscous oil which remains is
crystallized by trituration with diethyl ether. 7.7 g (89% of theory) of
1-[2-(2-chloroethoxy)phenoxy-sulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea
of melting point 132.degree.-134.degree. C. are obtained.
Example 3
3-(4,6-Dimethoxypyrimidin-2-yl)-1-(2-propargyloxyphenoxysulfonyl)urea
3.1 g (0.02 mol) of 2-amino-4,6-dimethoxypyrimidine are dissolved in 30 ml
of dichloromethane, and 5.1 g (0.02 mol) of 2-propargyloxyphenoxysulfonyl
isocyanate--dissolved in 20 ml of dichloromethane--are added at 0.degree.
C. After the reaction mixture has been stirred for 24 hours at room
temperature, it is diluted with 50 ml of dichloromethane, washed with 50
ml of 1N hydrochloric acid and 50 ml of water, dried and evaporated. The
oily residue crystallizes on trituration with diethyl ether. 7.4 g (91% of
theory) of
3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-propargyloxyphenoxysulfonyl)urea of
melting point 125.degree.-126.degree. C. are obtained.
Example 4
3-(4,6-Dimethoxypyrimidin-2-yl)-1-[2-(2-methoxyethoxy)phenoxysulfonyl]urea
1.74 g (0.0063 mol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate are
dissolved in 80 ml of acetonitrile, and 1.48 g (0.006 mol) of
2-(2-methoxyethoxy)phenyl sulfamate are added at room temperature. 1.0 g
(0.0066 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added and the
reaction mixture is then stirred at room temperature for 18 hours,
concentrated, diluted with H.sub.2 O and acidified with 2N hydrochloric
acid to give a pH of 3-4. After the solids have been filtered off with
suction and dried, 2.4 g (93% of theory) of
3-(4,6-dimethoxypyrimidin-2-yl)-1-[2-(2-methoxyethoxy)phenoxysulfonyl]urea
of melting point 106.degree.-108.degree. C. are obtained.
The compounds of the Tables which follow are prepared in an analogous
manner as described in Examples 1-4.
TABLE 1
__________________________________________________________________________
##STR13##
Ex. No.
R.sup.1 (R.sup.2).sub.n
R.sup.3 R.sup.5
R.sup.6
E n m.p. [.degree.C.]
__________________________________________________________________________
5 CH.sub.2 CH.sub.2 Cl
H CH.sub.3
CH.sub.3
CH 0
6 " H OCH.sub.3
CH.sub.3
CH 0
7 " H CH.sub.3
CH.sub.3
N 0
8 " H OCH.sub.3
CH.sub.3
N 0
9 " H OCH.sub.3
OCH.sub.3
N 0
10 " H OCH.sub.3
Cl CH 0
11 " H OCF.sub.2 H
CH.sub.3
CH 0
12 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
13 " H OCH.sub.3
Br CH 0
14 " H CH.sub.3
Cl CH 0
15 " H OCH.sub.3
H CH 0
16 " H OCH.sub.3
NHCH.sub.3
CH 0
17 " H OCH.sub.3
NHCH.sub.3
N 0
18 " H CH.sub.3
NHCH.sub.3
CH 0
19 " H CH.sub.3
NHCH.sub.3
N 0
20 " H OCH.sub.3
SCH.sub.3
CH 0
21 " H OCH.sub.3
OC.sub.2 H.sub.5
CH 0
22 " H OCH.sub.3
OC.sub.3 H.sub.7
CH 0
23 " H OCH.sub.3
OC.sub.2 H.sub.5
N 0
24 " H Cl OC.sub.2 H.sub.5
CH 0
25 " H OC.sub.2 H.sub.5
OC.sub.2 H.sub.5
CH 0
26 " H C.sub.2 H.sub.5
OCH.sub.3
CH 0
27 " H CF.sub.3
OCH.sub.3
CH 0
28 " H OCH.sub.2 CF.sub.3
CH.sub.3
CH 0
29 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
30 " H OCH.sub.2 CF.sub.3
OCH.sub.2 CF.sub.3
CH 0
31 " H OCH.sub.2 CF.sub.3
NHCH.sub.3
CH 0
32 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
33 " H OCH.sub.2 CF.sub.3
NHCH.sub.3
N 0
34 " H OCH.sub.3
NHC.sub.2 H.sub.5
CH 0
35 " H OCH.sub.2 CF.sub.3
NHC.sub.2 H.sub.5
CH 0
36 " H OCH.sub.3
N(CH.sub.3).sub.2
CH 0
37 " H OCH.sub.3
CH(OCH.sub.3).sub.2
CH 0
38 CH.sub.2 CH.sub.2 OCH.sub.3
H CH.sub.3
CH.sub.3
CH 0 103-105
39 " H OCH.sub.3
CH.sub.3
CH 0
40 " H CH.sub.3
CH.sub.3
N 0
41 " H OCH.sub.3
CH.sub.3
N 0
42 " H OCH.sub.3
OCH.sub.3
N 0
43 " H OCH.sub.3
Cl CH 0 Resin
44 " H OCF.sub.2 H
CH.sub.3
CH 0
45 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
46 " H OCH.sub.3
Br CH 0
47 " H CH.sub.3
Cl CH 0
48 " H OCH.sub.3
H CH 0
49 " H OCH.sub.3
NHCH.sub.3
CH 0
50 " H OCH.sub.3
NHCH.sub.3
N 0
51 " H CH.sub.3
NHCH.sub.3
CH 0
52 " H CH.sub.3
NHCH.sub.3
N 0
53 " H OCH.sub.3
SCH.sub.3
CH 0
54 " H OCH.sub.3
OC.sub.2 H.sub.5
CH 0
55 " H OCH.sub.3
OC.sub.3 H.sub.7
CH 0
56 " H OCH.sub.3
OC.sub.2 H.sub.5
N 0
57 " H Cl OC.sub.2 H.sub.5
CH 0
58 " H OC.sub.2 H.sub.5
OC.sub.2 H.sub.5
CH 0
59 " H C.sub.2 H.sub.5
OCH.sub.3
CH 0
60 " H CF.sub.3
OCH.sub.3
CH 0
61 " H OCH.sub.2 CF.sub.3
CH.sub.3
CH 0
62 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
63 " H OCH.sub.2 CF.sub.3
OCH.sub.2 CF.sub.3
CH 0
64 CH.sub.2 CH.sub.2 OCH.sub.3
H OCH.sub.2 CF.sub.3
NHCH.sub.3
CH 0
65 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
66 " H OCH.sub.2 CF.sub.3
NHCH.sub.3
N 0
67 " H OCH.sub.3
OCH.sub.3
CH 0
68 " H OCH.sub.2 CF.sub.3
NHC.sub.2 H.sub.5
CH 0
69 " H OCH.sub.3
N(CH.sub.3).sub.2
CH 0
70 " H OCH.sub.3
CH(OCH.sub.3).sub.2
CH 0
71 CH.sub.2 CHCH.sub.2
H CH.sub.3
CH.sub.3
CH 0 128-133
72 " H OCH.sub.3
CH.sub.3
CH 0 89-90
73 " H CH.sub.3
CH.sub.3
N 0
74 " H OCH.sub.3
CH.sub.3
N 0 112-115
75 " H OCH.sub.3
OCH.sub.3
N 0
76 " H OCH.sub.3
Cl CH 0
77 " H OCF.sub.2 H
CH.sub.3
CH 0
78 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
79 " H OCH.sub.3
Br CH 0
80 " H CH.sub.3
Cl CH 0
81 " H OCH.sub.3
H CH 0
82 " H OCH.sub.3
NHCH.sub.3
CH 0
83 " H OCH.sub.3
NHCH.sub.3
N 0
84 " H OCH.sub.3
OCH.sub.3
CH 0 123
85 " H CH.sub.3
NHCH.sub.3
N 0
86 " H OCH.sub.3
SCH.sub.3
CH 0
87 " H OCH.sub.3
OC.sub.2 H.sub.5
CH 0
88 " H OCH.sub.3
OC.sub.3 H.sub.7
CH 0
89 " H OCH.sub.3
OC.sub.2 H.sub.5
N 0
90 " H Cl OC.sub.2 H.sub.5
CH 0
91 " H OC.sub.2 H.sub.5
OC.sub.2 H.sub.5
CH 0
92 " H C.sub.2 H.sub.5
OCH.sub.3
CH 0
93 " H CF.sub.3
OCH.sub.3
CH 0
94 " H OCH.sub.2 CF.sub.3
CH.sub.3
CH 0
95 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
96 CH.sub.2 CHCH.sub.2
H OCH.sub.2 CF.sub.3
OCH.sub.2 CF.sub.3
CH 0
97 " H OCH.sub.2 CF.sub.3
NHCH.sub.3
CH 0
98 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
99 " H OCH.sub.2 CF.sub.3
NHCH.sub.3
N 0
100 " H OCH.sub.3
NHC.sub.2 H.sub.5
CH 0
101 " H OCH.sub.2 CF.sub.3
NHC.sub.2 H.sub.5
CH 0
102 " H OCH.sub.3
N(CH.sub.3).sub.2
CH 0
103 " H OCH.sub.3
CH(OCH.sub.3).sub.2
CH 0
104 CH.sub.2 CCH H OCH.sub.3
Cl N 0
105 " H CH.sub.3
CH.sub.3
CH 0 128-133
(decomp.)
106 " H OCH.sub.3
CH.sub.3
CH 0 143-146
107 " H CH.sub.3
CH.sub.3
N 0
108 " H OCH.sub.3
CH.sub.3
N 0
109 " H OCH.sub.3
OCH.sub.3
N 0
110 " H OCH.sub.3
Cl CH 0
111 " H OCF.sub.2 H
CH.sub.3
CH 0
112 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
113 " H OCH.sub.3
Br CH 0
114 " H CH.sub.3
Cl CH 0
115 " H OCH.sub.3
H CH 0
116 " H OCH.sub. 3
NHCH.sub.3
CH 0
117 " H OCH.sub.3
NHCH.sub.3
N 0
118 " H CH.sub.3
NHCH.sub.3
CH 0
119 " H CH.sub.3
NHCH.sub.3
N 0
120 " H OCH.sub.3
SCH.sub.3
CH 0
121 " H OCH.sub.3
OC.sub.2 H.sub.5
CH 0
122 " H OCH.sub.3
OC.sub.3 H.sub.7
CH 0
123 " H OCH.sub.3
OC.sub.2 H.sub.5
N 0
124 " H Cl OC.sub.2 H.sub.5
CH 0
125 " H OC.sub.2 H.sub.5
OC.sub.2 H.sub.5
CH 0
126 " H C.sub.2 H.sub.5
OCH.sub.3
CH 0
127 CH.sub.2 CCH H CF.sub.3
OCH.sub.3
CH 0
128 " H OCH.sub.2 CF.sub.3
CH.sub.3
CH 0
129 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
130 " H OCH.sub.2 CF.sub.3
OCH.sub.2 CF.sub.3
CH 0
131 " H OCH.sub.2 CF.sub.3
NHCH.sub.3
CH 0
132 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
133 " H OCH.sub.2 CF.sub.3
NHCH.sub.3
N 0
134 " H OCH.sub.3
NHC.sub.2 H.sub.5
CH 0
135 " H OCH.sub.2 CF.sub.3
NHC.sub.2 H.sub.5
CH 0
136 " H OCH.sub.3
N(CH.sub.3).sub.2
CH 0
137 " H OCH.sub.3
CH(OCH.sub.3).sub.2
CH 0
138 CH.sub.2 CClCH.sub.2
H OCH.sub.3
OCH.sub.3
CH 0
139 " H OCH.sub.3
CH.sub.3
CH 0
140 " H OCH.sub.3
CH.sub.3
N 0
141 " H OCH.sub.3
OCH.sub.3
N 0
142 " H OCH.sub.3
Cl CH 0
143 " H OCF.sub.2 H
CH.sub.3
CH 0
144 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
145 " H OCH.sub.3
NHCH.sub.3
CH 0
146 " H Cl OC.sub.2 H.sub.5
CH 0
147 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
148 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
149 CH.sub.2 CHCHCl H OCH.sub.3
OCH.sub.3
CH 0
150 " H OCH.sub.3
CH.sub.3
CH 0
151 " H OCH.sub.3
CH.sub.3
N 0
152 " H OCH.sub.3
OCH.sub.3
N 0
153 " H OCH.sub.3
Cl CH 0
154 " H OCF.sub.2 H
CH.sub.3
CH 0
155 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
156 " H OCH.sub.3
NHCH.sub.3
CH 0
157 " H Cl OC.sub.2 H.sub.5
CH 0
158 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
159 CH.sub.2 CHCl H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
160 CH.sub.2 C(CH.sub.3)CH.sub.2
H OCH.sub.3
OCH.sub.3
CH 0
161 " H OCH.sub.3
CH.sub.3
CH 0
162 " H OCH.sub.3
CH.sub.3
N 0
163 " H OCH.sub.3
OCH.sub.3
N 0
164 " H OCH.sub.3
Cl CH 0
165 " H OCF.sub.2 H
CH.sub.3
CH 0
166 " H OCF.sub.2 H
CF.sub.2 H
CH 0
167 " H OCH.sub.3
NHCH.sub.3
CH 0
168 " H Cl OC.sub.2 H.sub.5
CH 0
169 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
170 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
171 CH.sub.2 CHCHCH.sub.3
H OCH.sub.3
OCH.sub.3
CH 0
172 " H OCH.sub.3
CH.sub.3
CH 0
173 " H OCH.sub.3
CH.sub.3
N 0
174 " H OCH.sub.3
OCH.sub.3
N 0
175 " H OCH.sub.3
Cl CH 0
176 " H OCF.sub.2 H
CH.sub.3
CH 0
177 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
178 " H OCH.sub.3
NHCH.sub.3
CH 0
179 " H Cl OC.sub.2 H.sub.5
CH 0
180 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
181 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
182 CH.sub.2 CCCH.sub.3
H OCH.sub.3
OCH.sub.3
CH 0
183 " H OCH.sub.3
CH.sub.3
CH 0
184 " H OCH.sub.3
CH.sub.3
N 0
185 " H OCH.sub.3
OCH.sub.3
N 0
186 " H OCH.sub.3
Cl CH 0
187 " H OCF.sub.2 H
CH.sub.3
CH 0
188 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
189 " H OCH.sub.3
NHCH.sub.3
CH 0
190 " H Cl OC.sub.2 H.sub.5
CH 0
191 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
192 CH.sub.2 CCCH.sub.3
H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
193 CH.sub.2 CH.sub.2 Br
H OCH.sub.3
OCH.sub.3
CH 0
194 " H OCH.sub.3
CH.sub.3
CH 0
195 " H OCH.sub.3
CH.sub.3
N 0
196 " H OCH.sub.3
OCH.sub.3
N 0
197 " H OCH.sub.3
Cl CH 0
198 " H OCF.sub.2 H
CH.sub.3
CH 0
199 " H OCF.sub.2 H
OCF.sub.2 H
CH 0
100 " H OCH.sub.3
NHCH.sub.3
CH 0
101 " H Cl OC.sub.2 H.sub.5
CH 0
102 " H OCH.sub.2 CF.sub.3
OCH.sub.3
CH 0
203 " H OCH.sub.2 CF.sub.3
OCH.sub.3
N 0
204 CH.sub.2 CH(OCH.sub.3).sub.2
H OCH.sub.3
OCH.sub.3
CH 0
205 " H OCH.sub.3
CH.sub.3
CH 0
206 " H OCH.sub.3
CH.sub.3
N 0
207 C.sub.6 H.sub.5 H OCH.sub.3
OCH.sub.3
CH 0 117-119
208 " H OCH.sub.3
CH.sub.3
CH 0 138-139
209 " H OCH.sub.3
CH.sub.3
N 0 120-122
210 " H CH.sub.3
Cl CH 0 147-148
211 " H OCH.sub.3
Cl CH 0
212 " H CH.sub. 3
CH.sub.3
CH 0 136-138
213 CF.sub.2 CHFCF.sub.3
H OCH.sub.3
OCH.sub.3
CH 0 122-124
214 " H OCH.sub.3
CH.sub.3
CH 0
215 " H Cl OCH.sub.3
CH 0 160-162
216 " H OCH.sub.3
CH.sub.3
N 0
217 " H OCH.sub.3
CH.sub.3
CH.sub.3
0 Resin
218 CH.sub.2 C.sub.6 H.sub.5
H OCH.sub.3
OCH.sub.3
CH 0
219 " H OCH.sub.3
CH.sub.3
CH 0
220 CF.sub.2 CClFH H OCH.sub.3
Cl CH 0 106-110
221 CCH.sub.3 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH 0
222 " H OCH.sub.3
CH.sub.3
CH 0
223 " H OCH.sub.3
CH.sub.3
N 0
224 C.sub.5 H.sub.9 H OCH.sub.3
OCH.sub.3
CH 0
225 C.sub.5 H.sub.9 H OCH.sub.3
CH.sub.3
CH 0
226 CF.sub.2 CClFH H CH.sub.3
CH.sub.3
CH 0 63-66
227 " H OCH.sub.3
OCH.sub.3
CH 0 109-110
228 " H OCH.sub.3
CH.sub.3
CH 0
229 " H OCH.sub.3
CH.sub.3
N 0
230 CH.sub.2 CHCH.sub.2
6-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
231 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
232 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
N
233 CH.sub.2 CH.sub.2 Cl
6-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
234 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
235 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
N
236 CH.sub.2 CCH
6-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
237 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
238 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
N
239 CH.sub.2 CH.sub.2 OCH.sub.3
6-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
240 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
241 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
N
242 CH.sub.2 C.sub.6 H.sub.5
6-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
243 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
244 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
N
245 CCH.sub.3 CHCH.sub.2
6-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
246 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
247 " 6-CH.sub.3
H OCH.sub.3
CH.sub.3
N
248 C.sub.5 H.sub.9
6-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
249 C.sub.5 H.sub.9
6-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
250 C.sub.5 H.sub.9
6-CH.sub.3
H OCH.sub.3
CH.sub.3
N
251 CH.sub.2 CHCH.sub.2
5-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
252 CH.sub.2 CHCH.sub.2
5-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
253 CH.sub.2 CH.sub.2 Cl
5-CH.sub.3
H OCH.sub.3
CH.sub.3
N
254 " 5-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
255 CH.sub.2 CH.sub.2 OCH.sub.3 H
5-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
256 " 5-CH.sub.3
H OCH.sub.3
CH.sub.3
N
257 CH.sub.2 CCH
5-CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
258 " 5-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
259 CH.sub.2 CH.sub.2 Br
4-CH.sub.3
H OCH.sub.3
CH.sub.3
N
260 " 4-CH.sub.3
H OCH.sub. 3
OCH.sub.3
CH
261 CH.sub.2 CCCH.sub.3
3-CH.sub.3
H OCH.sub.3
CH.sub.3
CH
262 " 3-CH.sub.3
H OCH.sub.3
CH.sub.3
N
263 CH.sub.2 CHCH.sub.2
6-Cl H OCH.sub.3
OCH.sub.3
CH
264 " 6-Cl H OCH.sub.3
CH.sub.3
CH
265 " 6-Cl H OCH.sub.3
CH.sub.3
N
266 CH.sub.2 CH.sub.2 Cl
6-Cl H OCH.sub.3
OCH.sub.3
CH
267 " 6-Cl H OCH.sub.3
CH.sub.3
CH
268 " 6-Cl H OCH.sub.3
CH.sub.3
N
269 CH.sub.2 CCH
6-Cl H OCH.sub.3
OCH.sub.3
CH
270 " 6-Cl H OCH.sub.3
CH.sub.3
CH
271 " 6-Cl H OCH.sub.3
CH.sub.3
N
272 CH.sub.2 CH.sub.2 OCH.sub.3
6-Cl H OCH.sub.3
OCH.sub.3
CH
273 " 6-Cl H OCH.sub.3
CH.sub.3
CH
274 " 6-Cl H OCH.sub.3
CH.sub.3
N
275 CH.sub.2 CCH.sub.3CH.sub.2
6-Cl H OCH.sub.3
OCH.sub.3
CH
276 " 6-Cl H OCH.sub.3
CH.sub.3
CH
277 " 6-Cl H OCH.sub.3
CH.sub.3
N
278 C.sub.6 H.sub.5
6-Cl H OCH.sub.3
OCH.sub.3
CH
279 " 6-Cl H OCH.sub.3
CH.sub.3
CH
280 " 6-Cl H OCH.sub.3
CH.sub.3
N
281 CH.sub.2 CH(OCH.sub.3).sub.2
6-Cl H OCH.sub.3
OCH.sub.3
CH
282 " 6-Cl H OCH.sub.3
CH.sub.3
CH
283 " 6-Cl H OCH.sub.3
CH.sub.3
N
284 CH.sub.2 CHCH.sub.2
5-Cl H OCH.sub.3
OCH.sub.3
CH
285 " 5-Cl H OCH.sub.3
CH.sub.3
CH
286 CH.sub.2 CH.sub.2 Cl
4-Cl H OCH.sub.3
CH.sub.3
N
287 CH.sub.2 CH.sub.2 Cl
5-Cl H OCH.sub.3
OCH.sub.3
CH
288 CH.sub.2 CH.sub.2 OCH.sub.3
5-Cl OCH.sub.3
OCH.sub.3
CH
289 " 5-Cl H OCH.sub.3
CH.sub.3
N
290 CH.sub.2 CCH
5-Cl H OCH.sub.3
OCH.sub.3
CH
291 " 5-Cl H OCH.sub.3
CH.sub.3
CH
292 CH.sub.2 CHCHCl
4-Cl H OCH.sub.3
CH.sub.3
N
293 " 4-Cl H OCH.sub.3
OCH.sub.3
CH
294 CH.sub.2 C.sub.6 H.sub.5
3-Cl H OCH.sub.3
OCH.sub.3
CH
295 " 3-Cl H OCH.sub.3
CH.sub.3
N
296 CH.sub.2 CHCH.sub.2
6-F H OCH.sub.3
OCH.sub.3
CH
297 " 6-F H OCH.sub.3
CH.sub.3
CH
298 " 6-F H OCH.sub.3
CH.sub.3
N
299 CH.sub.2 H.sub.2 Cl
6-F H OCH.sub.3
OCH.sub.3
CH
300 " 6-F H OCH.sub.3
CH.sub.3
CH
301 " 6-F H OCH.sub.3
CH.sub.3
N
302 CH.sub.2 CCH
6-F H OCH.sub.3
OCH.sub.3
CH
303 " 6-F H OCH.sub.3
CH.sub.3
CH
304 " 6-F H OCH.sub.3
CH.sub.3
N
305 CH.sub.2 CH.sub.2 OCH.sub.3
6-F H OCH.sub.3
OCH.sub.3
CH
306 " 6-F H OCH.sub.3
CH.sub.3
CH
307 " 6-F H OCH.sub.3
CH.sub.3
N
308 CH.sub.2 CHCHCH.sub.3
6-F H OCH OCH.sub.3
CH
309 " 6-F H OCH.sub.3
CH.sub.3
CH
310 " 6-F H OCH.sub.3
CH.sub.3
N
311 CF.sub.2 CClFH
6-F H OCH.sub.3
OCH.sub.3
CH
312 " 6-F H OCH.sub. 3
CH.sub.3
CH
313 " 6-F H OCH.sub.3
CH.sub.3
N
314 CH.sub.2 CCCH.sub.3
6-F H OCH OCH CH
315 " 6-F H OCH.sub.3
CH.sub.3
CH
316 " 6-F H OCH.sub.3
CH.sub.3
N
317 CH.sub.2 CHCH.sub.2
5-F H OCH.sub.3
OCH.sub.3
CH
318 CH.sub.2 CHCH.sub.2
5-F H OCH.sub.3
CH.sub.3
CH
319 CH.sub.2 CH.sub.2 Cl
5-F H OCH.sub.3
CH.sub.3
N
320 " 5-F H OCH.sub.3
OCH.sub.3
CH
321 CH.sub.2 CH.sub.2 OCH.sub.3
5-F H OCH.sub.3
OCH.sub.3
CH
322 " 5-F H OCH.sub.3
CH.sub.3
N
323 CH.sub.2 CCH
5-F H OCH.sub.3
OCH.sub.3
CH
324 " 5-F H OCH.sub.3
CH.sub.3
CH
325 CH.sub.2 CH.sub.2 Br
4-F H OCH.sub.3
CH.sub.3
N
326 " 4-F H OCH.sub.3
OCH.sub.3
CH
327 C.sub.5 H.sub.9
3-F H OCH.sub.3
OCH.sub.3
CH
328 C.sub.5 H.sub.9
3-F H OCH.sub.3
CH.sub.3
N
329 CH.sub.2 CHCH.sub.2
6-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
330 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
331 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
332 CH.sub.2 CH.sub.2 Cl
6-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
333 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
334 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
335 CH.sub.2 CCH
6-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
336 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
337 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
338 CH.sub.2 CH.sub.2 OCH.sub.3
6-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
339 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
340 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
341 CH.sub.2 CHCHCH.sub.3
6-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
342 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
343 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
344 CH.sub.2 CHCHCl
6-COOCH.sub. 3
H OCH.sub.3
OCH.sub.3
CH
345 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
346 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
347 C.sub.6 H.sub.5
6-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
348 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
349 " 6-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
350 CH.sub.2 CHCH.sub.2
5-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
351 " 5-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
352 CH.sub.2 CH.sub.2 Cl
5-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
353 CH.sub.2 CH.sub.2 Cl
5-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
354 CH.sub.2 CH.sub.2 OCH.sub.3
5-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
355 " 5-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
356 CH.sub.2 CCH
5-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
357 " 5-COOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
358 CH.sub.2 CH.sub.2 Br
4-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
359 " 4-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
360 CH.sub.2 CClCH.sub.2
3-COOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
361 " 3-COOCH.sub.3
H OCH.sub.3
CH.sub.3
N
362 CH.sub.2 CHCH.sub.2
6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH
363 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
CH
364 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
N
365 CH.sub.2 CH.sub.2 Cl
6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH
366 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
CH
367 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
N
368 CH.sub.2 CCH
6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH
369 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
CH
370 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
N
371 CH.sub.2 CH.sub.2 OCH.sub.3
6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH
372 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
CH
373 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
N
374 CH.sub.2 CH.sub.3
6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH 131-132
375 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
CH 134-136
376 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
N
377 CH(CH.sub.3).sub.2
6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH
378 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
CH
379 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
N
380 CH.sub.2 CH.sub.2 CH.sub.3
6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH
381 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
CH
382 " 6-CH.sub.2 CHCH.sub.2
H OCH.sub.3
CH.sub.3
N
383 CH.sub.2 CHCH.sub.2
6-CH.sub.2 CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
384 " 6-CH.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
CH
385 CH.sub.2 CH.sub.2 Cl
6-CH.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
N
386 " 6-CH.sub.2 CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
387 CH.sub.2 CH.sub.2 OCH.sub.3
6-CH.sub.2 CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
388 CH.sub.2 CH.sub.2 OCH.sub.3
6-CH.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
N
389 CH.sub.2 CCH
6-CH.sub.2 CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
390 " 6-CH.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
CH
391 CH.sub.2 CH.sub.2 Br
6-CH.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
N
392 " 6-CH.sub.2 CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
393 CH.sub.2 CClCH.sub.2
6-CH.sub.2 CH.sub.3
H OCH.sub.3
OCH CH
394 " 6-CH.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
N
395 CH.sub.2 CHCH.sub.2
6-OCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
396 " 6-OCH.sub.3
H OCH.sub.3
CH.sub.3
CH
397 CH.sub.2 CH.sub.2 Cl
6-OCH.sub.3
H OCH.sub.3
CH.sub.3
N
398 " 6-OCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
399 CH.sub.2 CH.sub.2 OCH.sub.3
6-OCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
400 " 6-OCH.sub.3
H OCH.sub.3
CH.sub.3
N
401 CH.sub.2 CCH
6-OCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
402 " 6-OCH.sub.3
H OCH.sub.3
CH.sub.3
CH
403 CH.sub.2 CH.sub.2 Cl
6-OC.sub.6 H.sub.5
H OCH.sub.3
CH.sub.3
N
404 " 6-OC.sub.6 H.sub.5
H OCH.sub.3
OCH.sub.3
CH
405 CH.sub.2 CHCH.sub.2
6-OC.sub.6 H.sub.5
H OCH.sub.3
OCH.sub.3
CH
406 " 6-OC.sub.6 H.sub.5
H OCH.sub.3
CH.sub.3
N
407 CH.sub.2 CCH
6-OC.sub.6 H.sub.5
H OCH.sub.3
OCH.sub.3
CH
408 " 6-OC.sub.6 H.sub.5
H OCH.sub.3
CHHD 3 CH
409 CH.sub.2 CH.sub.2 OCH.sub.3
6-OC.sub.6 H.sub.5
H OCH.sub.3
CH.sub.3
N
410 " 6-OC.sub.6 H.sub.5
H OCH.sub.3
OCH.sub.3
CH
411 " 6-C.sub.6 H.sub.5
H OCH.sub.3
OCH.sub.3
CH
412 " 6-C.sub.6 H.sub.5
H OCH.sub.3
CH.sub.3
N
413 CH.sub.2 CCH
6-C.sub.6 H.sub.5
H OCH.sub.3
OCH.sub.3
CH
414 " 6-C.sub.6 H.sub.5
H OCH.sub.3
CH.sub.3
CH
415 CH.sub.2 CH.sub.2 Br
6-SO.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
N
416 " 6-SO.sub.2 CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
417 CH.sub.2 CClCH.sub.2
6-SO.sub.2 CH.sub.3
H OCH.sub.3
OCH.sub.3
CH
418 " 6-SO.sub.2 CH.sub.3
H OCH.sub.3
CH.sub.3
N
419 CH.sub.2 CHCH.sub.2
6-SOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
420 " 6-SOCH.sub.3
H OCH.sub.3
CH.sub.3
CH
421 CH.sub.2 CH.sub.2 Cl
6-SOCH.sub.3
H OCH.sub.3
CH.sub.3
N
422 " 6-SOCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
423 CH.sub.2 CH.sub.2 OCH.sub.3
6-SCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
424 " 6-SCH.sub.3
H OCH.sub.3
CH.sub.3
N
425 CH.sub.2 CCH
6-SCH.sub.3
H OCH.sub.3
OCH.sub.3
CH
426 " 6-SCH.sub.3
H OCH.sub.3
CH.sub.3
CH
427 CH.sub.2 CH.sub.2 Br
6-CF.sub.3
H OCH.sub.3
CH.sub.3
N
428 " 6-CF.sub.3
H OCH.sub.3
OCH.sub.3
CH
429 CH.sub.2 CClCH.sub.2
6-NO.sub.2
H OCH.sub.3
OCH.sub.3
CH
430 CH.sub.2 CH.sub.2 Cl
4,6-Cl.sub.2
H OCH.sub.3
Cl CH
431 " 4,6-Cl.sub.2
H OCH.sub.3
OCH.sub.3
432 " 4,6-Cl.sub.2
H OCH.sub.3
CH.sub.3
N
433 " 3,5-Cl.sub.2
H OCH.sub.3
OCH.sub.3
CH
434 CH.sub.2 CH.sub.2 OCH.sub.3
4,6-Cl.sub.2
H OCH.sub.3
Cl CH
435 " 4,6-F.sub.2
H OCH.sub.3
OCH.sub.3
CH
436 " 4,6-F.sub.2
H OCH.sub.3
CH.sub.3
CH
437 " 3,5-F.sub.2
H OCH.sub.3
OCH.sub.3
CH
438 CH.sub.2 CHCH.sub.2
4,6-F.sub.2
H OCH.sub.3
CH.sub.3
N
439 " 4,6-Cl.sub.2
H OCH.sub.3
OCH.sub.3
CH
440 " 4,6-Cl.sub.2
H OCH.sub.3
Cl CH
441 " 3,5-Cl.sub.2
H OCH.sub.3
OCH.sub.3
CH
442 CH.sub.2 C CH
4,6-Cl.sub.2
H OCF.sub.2 H
CH.sub.3
CH
443 " 4,6-F.sub.2
H OCH.sub.3
OCH.sub.3
CH
444 " 4,6-F.sub.2
H OCH.sub.3
CH.sub.3
N
445 " 3,5-F.sub.2
H OCH.sub.3
OCH.sub.3
CH
446 C.sub.6 H.sub.5
4,6-F.sub.2
H OCH.sub.3
Cl CH
447 " 4,6-Cl.sub.2
H OCH.sub.3
OCH.sub.3
CH
448 CH.sub.2 C.sub.6 H.sub.5
4,6-Cl.sub.2
H OCF.sub.2 H
OCF.sub.2 H
CH
449 " 4,6-F.sub.2
H OCH.sub.3
OCH.sub.3
CH
450 CH.sub.2 CHCHCH.sub.3
4,6-F.sub.2
H OCH.sub.3
CH.sub.3
N
451 " 4,6-Cl.sub.2
H OCH.sub.3
OCH.sub.3
CH
452 CH.sub.2 CHCHCl
4,6-Cl.sub.2
H OCH.sub.3
Cl CH
453 " 4,6-(CH.sub.3).sub.2
H OCH.sub.3
OCH.sub.3
CH
454 " 4,6-(NO.sub.2).sub.2
H OCH.sub.2 CF.sub.3
OCH.sub.3
CH
455 CH.sub.2 CH.sub.2 Cl
H CH.sub.3
OCH.sub.3
OCH.sub.3
CH
456 " H CH.sub.3
OCH.sub.3
CH.sub.3
N
457 " H CH.sub.2 CHCH.sub.2
OCH.sub.3
OCH.sub. 3
CH
458 " H CH.sub.2 CHCH.sub.2
OCH.sub.3
Cl CH
459 CH.sub.2 CH.sub.2 OCH.sub.3
H CH.sub.3
OCH.sub.3
OCH.sub.3
CH
460 " H CH.sub.3
OCH.sub.3
CH.sub.3
CH
461 " H CH.sub.2 CHCH.sub.2
OCH.sub.3
CH
462 " H CH.sub.2 CHCH.sub.2
OCH.sub.3
CH.sub.3
N
463 CH.sub.2 CHCH.sub.2
H CH.sub.3
OCH.sub.3
OCH.sub.3
CH
464 " H CH.sub.3
OCH.sub.3
Cl CH
465 " H CH.sub.2 CHCH.sub.2
OCH.sub.3
CH
466 " H CH.sub.2 CHCH.sub.2
OCF.sub.2 H
CH.sub.3
CH
467 CH.sub.2 CCH
H CH.sub.3
OCH.sub.3
OCH.sub.3
CH
468 " H CH.sub.3
OCH.sub.3
CH.sub.3
N
469 " H CH.sub.2 CHCH.sub.2
OCH.sub.3
OCH.sub.3
CH
470 " H CH.sub.2 CHCH.sub.2
OCH.sub.3
Cl CH
471 CH.sub.2 CCCH.sub.3
H CH.sub.3
OCH.sub.3
OCH.sub.3
CH
472 " H CH.sub.2 CHCH.sub. 2
OCF.sub.2 H
OCF.sub.2 H
CH
473 CH.sub.2 CHCHCl
H CH.sub.2 CHCH.sub.2
OCH.sub.3
OCH.sub.3
CH
474 " H CH.sub.3
OCH.sub.3
CH.sub.3
N
475 C.sub.6 H.sub.5
H C.sub.2 H.sub.5
OCH.sub.3
OCH.sub.3
CH
476 CH.sub.2 CH.sub.2 Br
H C.sub.2 H.sub.5
OCH.sub.3
Cl CH
477 CH.sub.2 CCH.sub.3CH.sub.2
H C.sub.2 H.sub.5
OCH.sub.3
OCH.sub.3
CH
478 CH.sub.2 CF.sub.3
H C.sub.2 H.sub.5
OCH.sub.2 CF.sub.3
OCH.sub.3
CH
479 CH.sub.2 CCH
H C.sub.2 H.sub.5
OCH.sub.3
OCH.sub.3
CH
480 CH.sub.2 C.sub.6 H.sub.5
6-CH.sub.3
CH.sub.3
OCH.sub.3
CH.sub.3
N
481 CH.sub.2 CH.sub.2 OCH.sub.3
6-OCH.sub.3
CH.sub.3
OCH.sub.3
OCH.sub.3
CH
482 CH.sub.2 CHCH.sub.2
6-Cl CH.sub.2 CHCH.sub.2
OCH.sub.3
Cl CH
483 CH.sub.2 CH(OCH.sub.3).sub.2
6-F CH.sub.2 CHCH.sub.2
OCH.sub.3
OCH.sub.3
CH
484 CH.sub.2 C CH
6-CF.sub.3
CH.sub.3
OCH.sub.2 CF.sub.3
OCH.sub.3
N
__________________________________________________________________________
TABLE 2
______________________________________
##STR14##
Ex. No. R.sup.1 (R.sup.2).sub.n
R.sup.5
m.p.
______________________________________
485 CH.sub.2 CHCH.sub.2
H CH.sub.3
486 " H H
487 " H OCH.sub.3
488 CH.sub.2 CH.sub.2 Cl
H OCH.sub.3
489 CH.sub.2 CH.sub.2 OCH.sub.3
H OCH.sub.3
490 CH.sub.2 CCH H OCH.sub.3
491 CH.sub.2 C.sub.6 H.sub.5
H OCH.sub.3
492 CH.sub.2 CHCHCl
H OCH.sub.3
493 CH.sub.2 CHCHCH.sub.3
H OCH.sub.3
494 CH.sub.2 CH.sub.2 Br
H OCH.sub.3
495 CH.sub.2 CCCH.sub.3
H OCH.sub.3
496 C.sub.5 H.sub.9
H OCH.sub.3
497 CH.sub.2 CHCH.sub.2
6-CH.sub.3
OCH.sub.3
498 CH.sub.2 CH.sub.2 Cl
6-OCH.sub.3
OCH.sub.3
499 CH.sub.2 CH.sub.2 OCH.sub.3
6-Cl OCH.sub.3
500 CH.sub.2 CHCH.sub.2
6-CF.sub.3
OCH.sub.3
501 CH.sub.2 CCH 6-F OCH.sub.3
502 CH.sub.2 CHCHCH.sub.3
6-OCF.sub.2 H
OCH.sub.3
______________________________________
TABLE 3
______________________________________
##STR15##
m.p.
Ex. No.
R.sup.1 R.sup.2 R.sup.5
G n [.degree.C.]
______________________________________
503 CH.sub.2 CHCH.sub.2
H CH.sub.3
CH.sub.2
0
504 " H H CH.sub.2
0
505 " H OCH.sub.3
CH.sub.2
0
506 CH.sub.2 CH.sub.2 Cl
H CH.sub.3
O 0
507 CH.sub.2 CH.sub.2 OCH.sub.3
H CH.sub.3
CH.sub.2
0
508 CH.sub.2 CCH H CH.sub.3
O 0
509 CH.sub.2 C.sub.6 H.sub.5
H CH.sub.3
CH.sub.2
0
510 CH.sub.2 CHCHCl
H CH.sub.3
O 0
511 CH.sub.2 CHCCH.sub.3
H CH.sub.3
CH.sub.2
0
512 CH.sub.2 CH.sub.2 Br
H CH.sub.3
O 0
513 CH.sub.2 CCCH.sub.3
H CH.sub.3
CH.sub.2
0
514 C.sub.5 H.sub.9
H CH.sub.3
O 0
515 CH.sub.2 CHCH.sub.2
6-CH.sub.3
CH.sub.3
CH.sub.2
1
516 CH.sub.2 CH.sub.2 Cl
6-OCH.sub.3
CH.sub.3
O 1
517 CH.sub.2 CH.sub.2 OCH.sub.3
6-Cl CH.sub.3
CH.sub.2
1
518 CH.sub.2 CHCH.sub.2
6-CF.sub.3
CH.sub.3
O 1
519 CH.sub.2 CCH 6-F CH.sub.3
CH.sub.2
1
520 CH.sub.2 CHCHCH.sub.3
6-OCF.sub.2 H
CH.sub.3
O 1
______________________________________
TABLE 4
______________________________________
##STR16##
Ex. No. R.sup.1 R.sup.2 R.sup.5
n m.p.
______________________________________
521 CH.sub.2 CHCH.sub.2
H CH.sub.3
0
522 " H H 0
523 " H OCH.sub.3
0
524 CH.sub.2 CH.sub.2 Cl
H CH.sub.3
0
525 CH.sub.2 CH.sub.2 OCH.sub.3
H CH.sub.3
0
526 CH.sub.2 CCH H CH.sub.3
0
527 CH.sub.2 C.sub.6 H.sub.5
H CH.sub.3
0
528 CH.sub.2 CHCHCl
H CH.sub.3
0
529 CH.sub.2 CHCHCH.sub.3
H CH.sub.3
0
530 CH.sub.2 CH.sub.2 Br
H CH.sub.3
0
531 CH.sub.2 C CCH.sub.3
H CH.sub.3
0
532 C.sub.5 H.sub.9
H CH.sub.3
0
533 CH.sub.2 CHCH.sub.2
6-CH.sub.3
CH.sub.3
1
534 CH.sub.2 CH.sub.2 Cl
6-OCH.sub.3
CH.sub.3
1
535 CH.sub.2 CH.sub.2 OCH.sub.3
6-Cl CH.sub.3
1
536 CH.sub.2 CHCH 6-F CH.sub.3
1
537 CH.sub.2 CCH 6-F CH.sub.3
1
538 CH.sub.2 CHCHCH.sub.3
6-OCF.sub.2 H
CH.sub.3
1
______________________________________
TABLE 5
______________________________________
##STR17##
Ex. No.
R.sup.1 R.sup.2 R.sup.5
R.sup.7
n m.p.
______________________________________
539 CH.sub.2 CHCH.sub.2
H CH.sub.3
CH.sub.3
0
540 " H H CH.sub.3
0
541 " H OCH.sub.3
CH.sub.3
0
542 CH.sub.2 CH.sub.2 Cl
H CH.sub.3
CH.sub.3
0
543 CH.sub.2 CH.sub.2 OCH.sub.3
H CH.sub.3
H 0
544 CH.sub.2 CCH H CH.sub.3
CH.sub.3
0
545 CH.sub.2 C.sub.6 H.sub.5
H CH.sub.3
H 0
546 CH.sub.2 CHCHCl
H CH.sub.3
CH.sub.3
0
547 CH.sub.2 CHCHCH.sub.3
H CH.sub.3
H 0
548 CH.sub.2 CH.sub.2 Br
H CH.sub.3
CH.sub.3
0
549 CH.sub.2 CCCH.sub.3
H CH.sub.3
H 0
550 C.sub.5 H.sub.9
H CH.sub.3
CH.sub.3
0
551 CH.sub.2 CHCH.sub.2
6-CH.sub.3
CH.sub.3
H 1
552 CH.sub.2 CH.sub.2 Cl
6-OCH.sub.3
CH.sub.3
CH.sub.3
1
553 CH.sub.2 CH.sub.2 OCH.sub.3
6-Cl CH.sub.3
H 1
554 CH.sub.2 CHCH.sub.2
6-CF.sub.3
CH.sub.3
CH.sub.3
1
555 CH.sub.2 CCH 6-F CH.sub.3
H 1
556 CH.sub.2 CHCHCH.sub.3
6-OCF.sub.2 H
CH.sub.3
CH.sub.3
1
______________________________________
TABLE 6
______________________________________
##STR18##
Ex.
No. R.sup.1 R.sup.2 R.sup.5
R.sup.6
E n m.p.
______________________________________
557 CH.sub.2 CHCH.sub.2
H OCH.sub.3
OCH.sub.3
CH 0
558 " H OCH.sub.3
CH.sub.3
CH 0
559 " H OCH.sub.3
CH.sub.3
N 0
560 CH.sub.2 CH.sub.2 Cl
H OCH.sub.3
CH.sub.3
CH 0
561 CH.sub.2 CH.sub.2 OCH.sub.3
H OCH.sub.3
CH.sub.3
N 0
562 CH.sub.2 CCH H OCH.sub.3
OCH.sub.3
CH 0
563 CH.sub.2 C.sub. 6 H.sub.5
H OCH.sub.3
CH.sub.3
N 0
564 CH.sub.2 CHCHCl
H OCH.sub.3
CH.sub.3
CH 0
565 CH.sub.2 CHCHCH.sub.3
H OCH.sub.3
OCH.sub.3
N 0
566 CH.sub.2 CH.sub.2 Br
H OCH.sub.3
CH.sub.3
CH 0
567 CH.sub.2 CCCH.sub.3
H OCH.sub.3
CH.sub.3
N 0
568 C.sub.5 H.sub.9
H OCH.sub.3
OCH.sub.3
CH 0
569 CH.sub.2 CHCH.sub.2
6-CH.sub.3
OCH.sub.3
CH.sub.3
N 1
570 CH.sub.2 CH.sub.2 Cl
6-OCH.sub.3
OCH.sub.3
CH.sub.3
CH 1
571 CH.sub.2 CH.sub.2 OCH.sub.3
6-Cl OCH.sub.3
OCH.sub.3
N 1
572 CH.sub.2 CHCH.sub.2
6-CF.sub.3
OCH.sub.3
CH.sub.3
CH 1
573 CH.sub.2 CCH 6-F OCH.sub.3
OCH.sub.3
N 1
574 CH.sub.2 CHCHCH.sub.3
6-OCF.sub.2 H
OCH.sub.3
CH.sub.3
CH 1
______________________________________
TABLE 7
______________________________________
##STR19##
Ex. No. R.sup.1 R.sup.2 R.sup.8
n m.p.
______________________________________
575 CH.sub.2 CHCH.sub.2
H OCH.sub.3
0
576 " H CH.sub.3
0
577 " 3-Cl CH.sub.3
0
578 CH.sub.2 CH.sub.2 Cl
H CH.sub.3
0
579 CH.sub.2 CH.sub.2 OCH.sub.3
H CH.sub.3
0
580 CH.sub.2 CCH H OCH.sub.3
0
581 CH.sub.2 CHCHCl
H CH.sub.3
0
582 CH.sub.2 CHCHCl
H CH.sub.3
0
583 CH.sub.2 CHCHCH.sub.3
H OCH.sub.3
0
584 CH.sub.2 CH.sub.2 Br
H CH.sub.3
0
585 CH.sub. 2 CCCH.sub.3
H CH.sub.3
0
586 C.sub.5 H.sub.11
H OCH.sub.3
0
587 CH.sub.2 CHCH.sub.2
6-CH.sub.3
CH.sub.3
1
588 CH.sub.2 CH.sub.2 Cl
6-OCH.sub.3
CH.sub.3
1
589 CH.sub.2 CH.sub.2 OCH.sub.3
6-Cl OCH.sub.3
1
590 CH.sub.2 CHCH.sub.2
6-CF.sub.3
CH.sub.3
1
591 CH.sub.2 CCH 6-F OCH.sub.3
1
592 CH.sub.2 CHCHCH.sub.3
6-OCF.sub.2 H
CH.sub.3
1
______________________________________
TABLE 8
______________________________________
##STR20##
Ex.
No. R.sup.1 R.sup.2 R7 R.sup.8
R.sup.11 n m.p.
______________________________________
593 CH.sub.2 CHCH.sub.2
HH OCH.sub.3
H0
594 " HH CH.sub.3
CH.sub.3 0
595 " HCH.sub.3 CH.sub.3
CH.sub.3 0
596 CH.sub.2 CH.sub.2 Cl
HH CH.sub.3
H0
597 CH.sub.2 CH.sub.2 OCH.sub.3
HH CH.sub.3
CH.sub.3 0
598 CH.sub.2 CCH HCH.sub.3 OCH.sub.3
CHF.sub.2 0
599 CH.sub.2 C.sub.6 H.sub.5
HH CH.sub.3
H0
600 CH.sub.2 CHCHCl
HH CH.sub.3
CH.sub.3 0
601 CH.sub.2 CHCHCH.sub.3
HCH.sub.3 OCH.sub.3
CH.sub.3 0
602 CH.sub.2 CH.sub.2 Br
HH CH.sub.3
H0
603 CH.sub.2 CCCH.sub.3
HH CH.sub.3
CH.sub.2 CF.sub.3 0
604 C.sub.5 H.sub.9
HCH.sub.3 OCH.sub.3
CH.sub.3 0
605 CH.sub.2 CHCH.sub.2
6-CH.sub.3 H
CH.sub.3
H1
606 CH.sub.2 CH.sub.2 Cl
6-OCH3 H CH.sub.3
CH.sub.3 1
607 CH.sub.2 CH.sub.2 OCH.sub.3
6-ClCH.sub.3
OCH.sub.3
CH.sub.3 1
608 CH.sub.2 CHCH.sub.2
6-CF.sub.3 H
CH.sub.3
H1
609 CH.sub.2 CCH 6-FH OCH.sub.3
CH.sub.3 1
610 CH.sub.2 CHCHCH.sub.3
6-ClCH.sub.3
CH.sub.3
CH.sub.3 1
______________________________________
BIOLOGICAL EXAMPLES
The damage on the weed plants and the tolerance by crop plants were scored
using a key where numbers from 0 to 5 express the activity. In this key
0 denotes no action
1 denotes 0-20% action or damage
2 denotes 20-40% action or damage
3 denotes 40-60% action or damage
4 denotes 60-80% action or damage
5 denotes 80-100% action or damage
1. Pre-emergence action on weeds
Seeds or rhizome pieces of monocotyledon and dicotyledon weed plants were
placed in plastic pots containing sandy loam soil and covered with soil.
Various dosages of aqueous suspensions or emulsions of the compounds
according to the invention formulated as wettable powders or emulsion
concentrates were then applied to the surface of the cover soil, at an
application rate of water of 600-800 l/ha (converted).
After the treatment, the pots were placed in the greenhouse and maintained
at good growth conditions for the weeds. Visual scoring of the damage to
plants or the emergence damage was carried out after the emergence of the
test plants after a trial period of 3 to 4 weeks, comparing them to
untreated control plants. As shown by the score data in Table 9, the
compounds according to the invention have good herbicidal pre-emergence
activity against a broad range of weed grasses and broad-leaf weeds.
2. Post-emergence action on weeds
Seeds or rhizome pieces of monocotyledon and dicotyledon weeds were placed
in plastic pots in sandy loam ground, covered with soil and grown in the
greenhouse under good growth conditions. Three weeks after sowing, the
test plants were treated in the three-leaf stage.
Various dosages of the compounds according to the invention formulated as
wettable powders or emulsion concentrates were sprayed onto the green
parts of the plants, at an application rate of water of 600-800 l/ha
(converted), and the action of the preparations was scored visually after
the test plants had remained in the greenhouse for about 3 to 4 weeks
under optimum growth conditions, comparing them to untreated control
plants.
The agents according to the invention exhibit a good herbicidal activity
against a broad range of economically important weed grasses and
broad-leaf weeds, also in the post-emergence treatment (Table 10).
3. Tolerance by crop plants
In further greenhouse experiments, seeds of a relatively large number of
crop plants and weeds were placed in sandy loam ground and covered with
soil.
Some of the pots were treated immediately as described under 1., those
remaining were placed in the greenhouse until the plants had developed two
to three true leaves and were then sprayed with various dosages of the
substances according to the invention as described under 2.
Four to five weeks after application, with the plants remaining in the
greenhouse, visual scoring revealed that the compounds according to the
invention did not cause any damage to dicotyledonous crops, such as, for
example, soya, cotton, rape, sugar beet and potatoes when applied both as
a pre-emergence and post-emergence treatment, even at high dosages of
active substance. Furthermore, Gramineae crops such as, for example,
barley, wheat, rye, sorghum millets, maize or rice, were also unaffected
by some of the substances. Thus, the compounds of the formula I exhibit
high selectivity on application for controlling undersired plant growth in
agricultural crops.
TABLE 9
______________________________________
Pre-emergence action of the compounds according
to the invention
Dosage in
Ex. No.
kg of herbicidal action
No. a.i./ha SIA CRS STM AS ECG LOM
______________________________________
2 0.6 5 5 5 1 4 3
3 0.6 5 5 5 2 5 2
4 0.6 5 5 5 1 3 2
71 0.6 5 5 3 3 4 4
74 0.6 5 5 4 1 3 1
84 0.6 5 5 5 1 3 1
______________________________________
TABLE 10
______________________________________
Post-emergence action of the compounds
according to the invention
Dosage in
Ex. No.
kg of herbicidal action
No. a.i./ha SIA CRS STM AS ECG LOM
______________________________________
2 0.6 5 5 5 1 4 1
3 0.6 5 5 5 1 4 2
4 0.6 5 4 4 1 4 2
71 0.6 5 4 4 3 4 3
74 0.6 5 5 5 1 3 2
84 0.6 5 5 5 0 5 3
______________________________________
Abbreviations:
SIA = Sinapis alba-
CRS = Chrysanthemum segetum-
STM = Stellaria media-
AS = Avena sativa-
ECG = Echinochloa crus-galli-
LOM = Lolium multiflorum-
a.i. = active substance
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